Oxygenated Tetrapyrroles Produced from Porphyrinogens

Lin, Wen Tai; Timkovich, Russell

doi:10.1006/bioo.1994.1006

Cited by 8 publications

(12 citation statements)

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“…2, structures 5 and 6) Lin and Timkovich (1994) described the isolation of a compound with a typical chlorin absorption spectrum following exposure of uroporphyrinogen I to bright sunlight. The compound was characterized by NMR as a hydroxyspirolactone derivative of uroporphyrin I.…”

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confidence: 99%

“…2, structures 7 and 8) These two compounds are derived by hydrolysis of an epoxide with oxygen inserted across the 7,8-positions of a β-pyrrolic ring. They were postulated to be the precursors of the hydroxyspirolactoneurochlorins (Lin and Timkovich, 1994) but have never been isolated or characterized. This is probably because although stable in solution, they are easily cyclized to the spirolactone structures during esterification with methanolic sulphuric acid.…”

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confidence: 99%

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High‐performance liquid chromatography/electrospray ionization tandem mass spectrometry of hydroxylated uroporphyrin and urochlorin derivatives formed by photochemical oxidation of uroporphyrinogen I

Danton

Lim

2007

Biomedical Chromatography

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Hydroxylated uroporphyrin I and urochlorin I derivatives formed by photochemical oxidation of uroporphyrinogen I were separated by high-performance liquid chromatography and fully characterized by electrospray ionization tandem mass spectrometry. The porphyrins and chlorins were identified by analysis of their product ion spectra with each hydroxylated derivative giving a characteristic collision-induced dissociation fragmentation pattern. The porphyrins and chlorins characterized were meso-hydroxyuroporphyrin I, alpha-hydroxypropionic acid uroporphyrin I, beta-hydroxypropionic acid uroporphyrin I, hydroxyacetic acid uroporphyrin I, trans-7-hydroxy-8-spirolactoneurochlorin I, cis-7-hydroxy-8-spirolactoneurochlorin I and trans- and cis-7,8-dihydroxyurochlorins I.

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High‐performance liquid chromatography/electrospray ionization tandem mass spectrometry of hydroxylated uroporphyrin and urochlorin derivatives formed by photochemical oxidation of uroporphyrinogen I

Danton

Lim

2007

Biomedical Chromatography

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“…The porphyrinogen and porphyrin differ by six mass units owing to saturation of the former macrocycle. Removal of an aliquot from the reaction mixture and treatment with I 2 (aqueous ethanol), a relatively clean method for oxidizing porphyrinogens Lin and Timkovich 1994), afforded the corresponding porphyrin 4 in 7.5% yield as determined by absorption spectroscopy. The ESI-MS spectrum following oxidation and purification exhibited a peak characteristic of the porphyrin (Fig.…”

Section: A Porphyrinogen Directly From Acyclic Materialsmentioning

confidence: 99%

Simple Formation of an Abiotic Porphyrinogen in Aqueous Solution

Lindsey

Ptaszek

Taniguchi

2009

Orig Life Evol Biosph

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Porphyrins have long been proposed as key ingredients in the emergence of life yet plausible routes for forming their essential pyrrole precursor have heretofore not been identified. Here we show that the anaerobic reaction of δ-aminolevulinic acid (ALA, 1-5 mM) with the β-ketoester methyl 4-methoxyacetoacetate (2-40 mM) in water (pH5-7) at 70-100°C for >6 h affords the porphyrinogen, which upon chemical oxidation gives the corresponding porphyrin in overall yield of up to 10%. The key intermediate is the α-methoxymethyl-substituted pyrrole, which undergoes tetramerization and macrocycle formation under kinetic control. The resulting type-I porphyrin bears four propionic acid and four carbomethoxy groups, is distinct from porphyrins (e.g., uroporphyrin or coproporphyrin) derivable from ALA alone via the extant universal biosynthetic path to tetrapyrroles, and is photoactive upon assembly into cationic micelles in aqueous solution. The simple self-organization of eight acyclic molecules into a tetrapyrrole macrocycle, from which a porphyrin is derived that is photoactive in lipid assemblies, augurs well for the spontaneous origin of catalysts and pigments essential for prebiotic metabolism and proto-photosynthesis.

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“…In porphyria cutanea tarda (PCT), the most common human porphyria, Uro-D activity is depressed, resulting in an accumulation of uroporphyrinogens (Elder, 2003). Uroporphyrinogen is unstable to air, especially in the presence of light, and is easily oxidized to uroporphyrin, accompanied by oxygenated uroporphyrin derivatives (Lin and Timkovich, 1994;Danton and Lim, 2007).…”

Section: Introductionmentioning

confidence: 99%

“…Oxygenated porphyrins have also been described by Lin and Timkovich (1994) following photo-oxidation of porphyrinogens. Since compounds with a porphomethene structure have not been identified in these studies, a more detailed examination of the products formed was carried out in order to confirm or refute the existence of such a derivative.…”

Section: Introductionmentioning

confidence: 99%

Porphomethene inhibitor of uroporphyrinogen decarboxylase: analysis by high‐performance liquid chromatography/electrospray ionization tandem mass spectrometry

Danton

Lim

2007

Biomedical Chromatography

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An uroporphomethene inhibitor of uroporphyrinogen decarboxylase, characterized by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry, was reported recently (Phillips et al., Proceedings of the National Academy of Sciences of the United States of America 2007; 104: 5079-5084). Close examination of the tandem mass spectrometric fragmentation pattern of the compound showed that it is not a tetrapyrrole or an uroporphyrinogen or uroporphyrin related molecule. The product ion spectrum showed a fragmentation pattern typical of a poly(ethylene glycol) structure. Characteristic fragmentations of the side-chain acetic acid and propionic acid substituents of a uroporphyrin or uroporphyrinogen derivative were absent.

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Oxygenated Tetrapyrroles Produced from Porphyrinogens

Cited by 8 publications

References 0 publications

High‐performance liquid chromatography/electrospray ionization tandem mass spectrometry of hydroxylated uroporphyrin and urochlorin derivatives formed by photochemical oxidation of uroporphyrinogen I

High‐performance liquid chromatography/electrospray ionization tandem mass spectrometry of hydroxylated uroporphyrin and urochlorin derivatives formed by photochemical oxidation of uroporphyrinogen I

Simple Formation of an Abiotic Porphyrinogen in Aqueous Solution

Porphomethene inhibitor of uroporphyrinogen decarboxylase: analysis by high‐performance liquid chromatography/electrospray ionization tandem mass spectrometry

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